Robbing the Cradle

by StormLuna

Rating: mature
Tags: Self Insert, Equestria Girls, Sex, Principal Celestia, Human, Romance, Vice-Principal Luna, Porn
Length: 4035

I am a senior at Canterlot High and I just recently turned 18. I have good grades, I have never gotten into any fights or did anything else bad so I was unnerved when Vice-Principal Luna called me into her office.

I am a senior at Canterlot High and I just recently turned 18. I have good grades, I have never gotten into any fights or did anything else bad so I was unnerved when Vice-Principal Luna called me into her office. Her reason for calling me in though was unorthodox and very surprising.

All characters in the story are age 18 or over.

Trigger warnings: Vice-Principal/Student fun, oral sex, vaginal sex, boobie sucking.

Published 2020-09-07 17:00:01 UTC
Last updated 2021-11-25 14:25:01 UTC

Intimate Bonding

It was another day at Canterlot High and classes were about to begin. While some students were never very enthusiastic about going to school, it was alright with me. Yeah, I only had a few friends and didn't really associate with the most popular kids in the school, I did get along with them when I had school projects with them.

It was a few days after my eighteenth birthday and given that I had never gotten into any fights during my whole time there, I had never been truant, tardy or anything else that would show up as something negative on my student record, I was surprised when I was called in to Vice-Principal Luna's office. The thing with Luna, she was the one who normally dished out punishments for bad behavior so being called in made me wonder what was up.

I remember when I walked in to her office, she was sitting with the back of her chair facing me. She had one of those chairs with a tall back so I couldn't tell what kind of mood she was in. That unnerved me a bit as I am one of those types that can tell someone's mood simply by how they are sitting. Once the door closed behind me, she got up and approached me. What I saw her wearing shocked me big time. What she was wearing left very little to the imagination at all.

She was the first to speak, "Oh Luke, you're here."

I asked, "Vice-Principal Luna, what is it? Did I do something wrong?"

She approached me further and stood to where we were face to face, right at eye level. She reached out, grabbed my hand and enthusiastically replied, "No, just the opposite actually! I did call you in here for a matter of great importance though."

Now when she grabbed my hand, I was perplexed. Why in the world would Vice-Principal Luna grab my hand? That reminded me of something that a kindergarten teacher would do to comfort a student who fell and skinned their knee to comfort them. She pointed towards a couch she had in her office and ordered, "Sit down, there is something I need to discuss with you."

Now why she would have a couch in her office is beyond me. I would expect a higher up in a school to just have their desk and two chairs on the other side of it for when a student and one of their parents would have to meet with her. I would be more shocked when she sat down right next to me, close enough that we were almost making contact.

She continued the conversation, "Luke, I'm sure you're wondering why I called you in." She put her arm around me and continued, "This is about something that dates back to a couple years ago, something involving you directly."

I was getting more nervous because why would she just now bring something like that up. I asked, "Something from a couple years ago? What is that?"

She replied, "I remember back then, during your sophomore year, that you had begun to briefly smile at me before you would quickly look away. At first I didn't think anything about it but as the behavior continued, I began to wonder why you always did that until one day I noticed you looked at one thing in particular."

I immediately became much more nervous because for quite some time, I would glance at her tits before looking up at her face and smiling. I just hoped that I wouldn't get suspended or expelled for checking Vice-Principal Luna out. She then removed her top, which was something that you'd normally see girls my age wearing to parties. She then removed her bra, completely exposing her sexy breasts. They weren't huge but they were still somewhat big and were nice and firm.

She pointed to them and continued, "I know you find these sexy." She grabbed my hand and moved it towards them. She added, "You can touch them if you like."

I was in a state of shock, here was Vice-Principal Luna letting me touch her tits. It felt kind of odd but at the same time it was really turning me on. I turned to where I was facing towards her, reached out and cupped them. She gave me a smile and continued, "They are really nice, aren't they."

I was in a daze and dreamily replied, "They're beautiful Vice-Principal Luna."

She turned to where she was facing me and looked down. She noticed, "My my Luke, I must really be turning you on!"

I gave her a blush and replied, "Uh, maybe!"

She pulled me up and suggested, "Since you've seen my girls, how about we show each other everything."

I was in a state of shock over her suggestion. She was wanting us to get naked, in her office! She headed to her office door and locked it. She gave me a smile and added, "There, now we won't have to worry about being caught."

I was still a bit apprehensive about it but did what she requested. Once she stripped down entirely, I was lost in her beauty. Seeing her fully nude was something that had popped up in plenty of my more erotic fantasies involving her, well it was part of what showed up anyway. I watched in further shock when she spread her legs wide and giggled, "Come here Luke, I know what runs through your fantasies."

With the sultry smile she gave me how could I possibly refuse? I got down on my hands and knees and began to suck on her feet before slowly moving my way up her legs. I could hear her gasping as I moved further on up and once I got above her knees, she grabbed me by the hair and moaned, "Oh yes, keep moving up Luke, keep moving up!"

I kept moving up and once I hit her inner thigh, I felt her womanhood make contact with my face and it was sopping wet. "She's aroused by me?" That caused me to be elated. Never once did I imagine that Vice-Principal Luna would be turned on by me.

When I finally moved in on her prize, she yanked my hair violently and quietly moaned, "Yes baby yes! Suck it, probe it!"

I did as requested and my goodness, she is so sweet! This was another one of my fantasies, eating her out. This was one thing that I never imagined would happen, especially in her office. I certainly wasn't going to complain about this at all. I would enjoy the moment and hope that all of this wasn't a dream.

As I continued to eat her, her moans began to become louder and her pulling of my hair became more intense. One thing I really worried about her moaning though was that we would likely get caught and I would hate to think of what would happen if we did. Chances are I would get expelled and Luna would get fired.

When her moaning became more intense and her breathing became heavier, I knew what was coming. I knew that the one meal I have fantasized about having for so long was about to happen. Soon she unloaded into my mouth and let out a somewhat loud moan. As it flooded into my mouth, I too let out a moan as it was the sweetest thing I had ever had.

Once I swallowed every last drop, I was thrilled that I had finally swallowed Vice-Principal Luna's cum. It was a fantasy of mine for so long and the taste of it was like a slice of heaven. She then grabbed me by the hair and pulled me up. She pushed my face into her bosom and giggled, "I know what you want next!"

I did want her tits very badly so I moved in and began to suck on them, gently at first. She let out soft moans as I started sucking on them and a gasp when I would flick my tongue up against her hard nipples. She used her hands to push my face further into them and gently moaned, "Oh yes Luke, you have no idea how badly I've wanted this from you."

When I heard that, I almost began to wonder if she hadn't been having fantasies about me too. I suppose I hadn't thought about it until she said that because she did smile back at me whenever I would take a quick glance at her and smile. Perhaps she called me in for this because now that I'm 18, this is perfectly legal. Yeah doing it in her office probably isn't but she couldn't get in trouble for seducing a minor now.

I couldn't help but suck harder and as I did, we both began to breathe harder. She had forced my face so deep into her bosom that there was not a ton of air but I didn't mind that at all. I was sucking on Luna's tits and I was in heaven at that moment. She would pull me out of her bosom too quickly though and soon I was standing at eye level with her again. She had a look of pure lust in her eyes as she said, "You know Luke, you've made me feel like a queen so far."

I asked, "Really?"

She replied, "Yes, you have."

We began to move in closer and opened our mouths as we began to kiss. Our first kiss was a wet, sloppy one, one just like in my fantasies about her. As our tongues began a love dance, I could feel her saliva flowing into my mouth and mine flowing into hers. I happily swallowed everything from her that flowed into my mouth.

As our kiss deepened, we began to moan gently and massage one another. First our massaging started on our backs and then we began to move down. When we began to massage the other's butt, our moaning became a bit louder but we knew that we couldn't just moan as loud as we would in a motel room or in her bedroom.

Finally Luna couldn't take it anymore, she broke the kiss and headed to the couch. She opened it up to reveal that it was one that folded out into a bed. I was beyond shocked when I saw this. I never imagined that anyone at a school would have a couch that would fold out into a bed. She pointed down at the bare mattress and ordered, "Sit down."

I did as ordered and she then draped herself around me. She looked into my eyes and began, "You know Luke, so far you have brought more pleasure into my life than anyone else ever has. I have long avoided doing things like this because no man has met what my sister calls sky high standards, until now. You have given me the kind of touch that has only existed in my fantasies and I will admit this, you are incredibly sexy."

"I am?" I gasped.

"Yes, you are." Luna continued, "I remember the first time you looked at me with that smile, I decided right then and there that I would not even attempt to get into any relationships until you were of legal age." She gave me a kiss before continuing, "And now here you are, of legal age, and you have brought me so much joy in just one morning." She kissed me again before asking, "Luke, would you be my boyfriend?"

I was in a state of shock. Here was the woman I had had so many lucid fantasies about and plenty of erotic dreams about asking me to be her boyfriend! I replied, "Of course I'll be your boyfriend! I love you so much Luna!"

"I love you too Luke." Luna replied. She then sprawled out on the bed and suggested "What do you say we consummate our relationship? What do you say we bond in the most intimate way?"

I agreed, "I would love that Luna. I do want to warn you though that I'm a virgin and I hope that I don't let you down."

Luna stroked my leg and replied, "I'm going to let you in on a secret, I'm a virgin too so this will be incredibly special for us. We will be the first ones we share our bodies with."

This was something that made me incredibly happy. I never once imagined that not only would I be giving Luna my virginity butt hat she would be giving me hers as well. Not only was I happy over that but also us being a couple now. Now the biggest thing would be us not being caught.

As she laid there all sprawled out, I readied myself to take her, I readied myself for us to share our bodies in the most intimate way. As I knelt over her, she gave me a nervous smile and requested, "Please be gentle, I've never done this before and I don't want us to be caught."

I gave her a smile and moved in on her. I looked down and saw her needy pussy awaiting my member. When I began to insert it into her, we both let out a gasp of delight. As I moved it further in she began to moan gently and once I had it all the way in her, I saw a slight grimace of pain on her face. I asked, "Luna, are you ok?"

Luna replied, "I'm fine, it is just that you're about to pop my cherry. Thrust me but be gentle please."

I began to thrust her and she let out a gasp of pain and I suddenly felt a pain in my back as she had sank her fingernails into me. I stopped and asked, "Are you sure you want to do this? I don't want to hurt you."

Luna begged, "Please do it Luke, but like I said, be gentle."

I again began to thrust her and with each thrust, she let out painful gasp after painful gasp until finally, those gasps changed from ones of pain to ones of delight. She then ordered, "Harder, faster, deeper!"

I complied with her request and very quickly we were both breathing heavily and our moaning became louder. Now I didn't want us to get caught so I began to kiss her passionately so our moaning would be more muffled. She soon wrapped her legs around mine and forced her knees up against my butt and was pushing on it, causing me to thrust her harder.

As I continued to thrust her, both of our bodies began to heat up and we were beginning to sweat. Feeling her sweaty body wrapped around mine was like a slice of heaven. I was doing my best to hold back my orgasm because I wanted to perform my absolute best for her given that this was our first time.

Eventually we clung to one another tighter, our breathing became heavier and our muffled moans became louder and louder until we let out one final moan as we climaxed simultaneously. The feeling of her cum flooding out of her, soaking my member felt so good and unloading into her was my ultimate fantasy come true. Like it was in all my dreams about her, we had sex and we wound up becoming a couple.

After we did the deed, we laid there looking into one another's eyes lovingly and began to kiss passionately. I could feel the love flowing between us and when she rolled me onto my back and deepened the kiss, filling my mouth full of her saliva making sure that I swallowed every last drop of it.

With her being on top of me, I felt like I was on top of the world. I'm going to admit, I fantasized that Luna would be on top of me a lot and even the thoughts of her being the dominant one in the relationship not only made me incredibly hot but it was what I was hoping for.

After she broke the kiss she began, "You know Luke, given that I'm ten years older than you, I'll be the dominant one in the relationship."

I gave her a huge smile, "Believe it or not but I was hoping for that. In every single fantasy I've had about you, which are many, you are the dominant one, you often own me."

Luna gave me another kiss before continuing, "Well then, I think we will get along just fine!" She then let out a yawn, "I don't know about you but I'm tired. What do you say we get some rest?"

I agreed, "I would love that Luna."

We rolled onto our sides and wrapped our bodies tightly together. I never once imagined that this would happen with Luna, especially in her office. One thing I did know is that I hoped that we could do this often, very often. Even if she demanded that I spend whole weekends with her, I would gladly do it. She is my girlfriend after all and I would do anything to make the one I love happy.

Epilogue: Busted!

Epilogue: Busted!

Several hours had passed after the two of us had fallen asleep holding one another tight when we both came to. We opened our eyes and looked lovingly at one another. Luna was the first to say anything, "You know Luke, I hope that a time will come when this is what we wake up to every single day."

I replied, "I would love that Luna, I would love that more than anything."

We again began to kiss one another passionately and that would ultimately turn into something else, something that was yet another fantasy of mine. She forced me onto my back and ordered, "Spread your legs wide for me."

I did as complied and when she began to lower herself towards my fully erect member, I was thrilled. Luna was about to "ride the bishop" as some call it and that was yet another fantasy of mine. It almost seemed like she knew about my fantasies, like she was a mind reader.

Once she began to ride me, both of us began to moan loudly. I was mesmerized by those sexy tits of hers bouncing. I was able to reach up and grope them as she continued to bounce up and down on me. The more she bounced on me, the louder our moaning became. I was absolutely loving how she continued to bounce up and down on me with more and more force.

I was trying my hardest to hold back my orgasm but given that I had the hottest woman in the world giving it to me like this, I had a feeling that it would come all too soon. It did come quicker than I would like but again we both climaxed simultaneously but unlike last time, we both let out loud, unmuffled moans. Once we had climaxed, she collapsed down on me and exclaimed, "Oh Luke, I could just ride you forever and ever!"

I too exclaimed, "Luna, I would be more than happy to let you."

We again began to kiss passionately until we heard someone snickering. We looked up to see Principal Celesta standing there, with a smirk on her face. "So sister, I see you finally took the one you've been going on and on about for two years!"

I asked, "Really, she's been talking about me for two years?"

Celestia sat down by us and giggled, "Oh yes! She told me about the first time when you caught a glimpse of her girls and then smiled at her." She leaned down towards me and added, "And ever since then, she went on about how when you came of legal age, that she was going to bag you!"

I turned to Luna and asked, "Seriously, you've wanted to bag me for that long?"

Luna replied, "Yes. I'll admit, I have probably stared at you a lot more than I should have but whenever you'd do that, I'd get a warm feeling knowing that someone thought I was hot."

I gasped, "Really?"

Luna replied, "Really!"

One thing neither one of us had noticed is that Celestia had begun to undress. As she was undressing she looked to Luna and asked, "You know, you really should share him with me. After all, every young man's dream come true is to have a hot woman on each arm!" She turned to me and asked, "Isn't that right?"

I will admit, Principal Celestia is hot, not as hot as Luna, but I have bonded with Luna in a truly special way, a way that I had not her. I replied, "Principal Celestia, it is not that way with all men. Luna and I have become a couple and she is special to me. I am not like that, a real man sticks to one woman and one woman alone." I gave Luna a smile and added, "And for me, that woman is Luna."

Luna suggested, "Sister, if you want one of the students I'm sure you can find one of legal age who checks you out all the time."

This gave me an idea, an idea that would cause Celestia to drop all this. I suggested, "Principal Celestia, I have a friend that goes by the name of Sunrise. I'm not sure if you're into women or not but if you are, she is of legal age and goes on and on about how hot you are."

Celestia's eyes lit up when I brought her up. She embraced me and exclaimed, "Really, this friend of yours thinks I'm hot?"

I replied, "Yes so I would advise that you just let Luna and I be and go make plans on calling her into your office tomorrow morning."

Luna added, "And don't worry sister, I won't even come barging into your office when you two are getting it on!"

Celestia let go of me and began to get dressed. She looked at us and began, "Luna, I'm sorry for suggesting that you share your boyfriend. It is obvious that he truly loves you and you deserve the best." She then focused more on me and added, "And I know you will be good for my sister. Yes you are just barely legal but it is obvious that you have the maturity that it takes to be loyal. Your peers would likely jump on the chance to have both of us with him."

In unison we replied, "Thanks." Luna then added, "Now go get ready to woo Sunrise into your office!"

Celestia replied, "Oh I will!"

Once Celestia was fully dressed, she left us alone in Luna's office. Luna gave me a loving smile and said, "Luke, I find it admirable that you would only choose me. Like my sister said, your peers would likely choose both of us but like a real man, you chose the one you fell in love with."

I replied, "Luna, it is just how I am. I have loved you for a long time and we were finally able to become a couple. I am not the type that believes in open relationships, sharing in relationships or anything else that does not relate with loyalty."

Luna gave me a deep kiss before sprawling out on the bed and suggesting, "Shall we have round three?"

I returned the kiss and replied, "Yes, let's do. I love you so much Luna!"

Luna said, "I love you too Luke."

I was happy that Celestia dropped it right away when both of us objected to her having me too. I'm sure both of us were happy that Celestia didn't use this as a way to blackmail Luna into sharing me and one thing I do hope is that Celestia will want to hook up with Sunrise. She is a good but shy girl and I know that if things work out with Celestia, they'll both be happier.